Ask a resistant manager for more flexible working

You want more flexibility over where or when you work, and your manager has said no before. This rewrites your request three ways, assertive that frames flexibility as reasonable, diplomatic that addresses their known worries head on, and a middle version, with your proposed arrangement built in. For making the ask land with someone already wary of it.

I want to ask my manager for more flexibility in where or when I work, and they have been resistant before.

Manager's known concerns: {MANAGER_CONCERNS}
Flexibility I am requesting: {FLEXIBILITY_REQUEST}
How I plan to make it work: {PROPOSED_ARRANGEMENT}
My draft message: {MESSAGE_DRAFT}

Rewrite this message in three versions:
1. Assertive: states the request clearly and frames flexibility as a reasonable expectation
2. Diplomatic: leads with understanding the manager's concerns, then makes the case with reassurances
3. Neutral: presents it as a trial proposal with clear success criteria, no pressure either way

Label each version clearly. Keep all three under 150 words each. End with one sentence on how each tone might land with a cautious manager.